Season 2 Episode 4 | 2.26.2026

Money Changes the Deal With Geoffrey Kent

Many entrepreneurs treat funding as a growth decision. Geoffrey Kent explains why that mindset leads to wasted time and failed businesses. Raising money is about managing risk — your time, your ownership, your reputation, and your future flexibility. In this conversation, Geoffrey breaks down why most founders pitch the wrong investors, misunderstand what lenders actually want, and fail to prepare financially before seeking capital.
The episode dives deep into debt vs. equity, smart money vs. dumb money, angel investors vs. venture capital, and how crowdfunding fits into early-stage funding. Geoffrey also explains why your financial assumptions matter more than your pitch deck, how investors evaluate deals in seconds, and why an early “no” may be the best outcome. This episode equips entrepreneurs to approach funding strategically — and avoid deals they’ll spend years trying to unwind.

Key Takeaways● Funding Is About Risk First – Before thinking about growth, understand the time, control, and reputation risk attached to capital.● Debt and Equity Are Not the Same – Debt keeps ownership but requires cash flow or collateral. Equity brings partners but costs ownership.● Smart Money Beats Dumb Money – The right investor brings advice, connections, and opportunity — not just a check.● Your Stage Determines Your Investor – Startups, growth companies, and expansion-stage businesses require different types of funding partners.● Assumptions Drive Everything – Strong financial assumptions make your numbers defensible and your deal credible.● Early “No” Saves Time – Rejection from the wrong investor prevents wasted months chasing the wrong capital.● Crowdfunding Is More Powerful Than You Think – With the right story and structure, it can validate demand and raise meaningful capital.
Sound Bites● "Funding is never a one-time event." – Geoffrey Kent● "The people who get funding match their deal to people predisposed to do that deal." – Geoffrey Kent● "If they throw your business plan in the trash early, they’re doing you a favor." – Geoffrey Kent● "Rate of return is the first thing an investor cares about." – Geoffrey Kent● "You don’t want someone to just give you money. You want them invested in your success." – Sean M. Atkinson● "The more you understand how finance works, the stronger you become as an entrepreneur." – Geoffrey Kent
Projects:Entrepreneur Academy
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📌 Timestamps:00:00 Understanding the Funding Landscape
03:36 The Risks of Funding Decisions
11:57 Debt vs. Equity: Making Informed Choices
21:33 Strategic Planning for Funding Success
24:07 Leveraging Credit for Business Growth
28:09 Strategic Partnerships and Larger Contracts
28:11 Understanding Equity Financing
33:18 Navigating Angel Investors and Venture Capital
37:20 The Importance of Crowdfunding
49:40 Exploring Debt Crowdfunding
50:46 Crowdfunding and Structuring Loans
54:15 The Importance of Storytelling in Fundraising
59:46 Understanding Funding Stages
01:07:48 The Role of Fear in Deal Structuring
01:14:28 Building Relationships with Investors
01:15:56 The Power of Persistence in Entrepreneurship
01:16:25 Strategic Partnerships vs. Funding
01:16:28 Scaling Through Strategic Alliances
01:17:02 The Importance of Financial Literacy for Entrepreneurs
01:20:12 Episode 2 Outro.mp4

Geoffrey Kent

Geoffrey is a serial entrepreneur (having launched 20+ entrepreneurial ventures over the last 5 decades), who took his last tech venture (Cognis IT) from launch to successful exit in 6 years over a decade ago. In addition to an MBA in Entrepreneurial Management from the Wharton School of Business at the University of Pennsylvania, Geoffrey has been an executive at Xerox Corporation, AT&T, the Erving Group (a holding company owned by NBA Hall of Famer Julius “Dr. J” Erving), and Deloitte Consulting, has taught entrepreneurship at Lincoln University, has judged Drexel University’s annual business plan competition, and has served on multiple corporate boards of directorships. Geoffrey now teaches entrepreneurs how to build fundable plans that get the money they need to grow their business and exit when and how they want to.
Website: Think Big with Geoffrey Kent